(5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride

• ChemBase ID: 176210
• Molecular Formular: C19H25ClN2O
• Molecular Mass: 332.8676
• Monoisotopic Mass: 332.16554111
• SMILES: c12c3cccc1C(=O)N(C[C@H]2CCC3)[C@@H]1C2CCN(C1)CC2.Cl
• Canonical SMILES: O=C1N(C[C@@H]2c3c1cccc3CCC2)[C@H]1CN2CCC1CC2.Cl
• InChI: InChI=1S/C19H24N2O.ClH/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20;/h2,4,6,13,15,17H,1,3,5,7-12H2;1H/t15-,17+;/m1./s1
• InChIKey: OLDRWYVIKMSFFB-KALLACGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• IUPAC Traditional name: (5S)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• Synonyms: (3aS)-2-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one Hydrochloride; RS 25233-197; (S,R)-Palonosetron Hydrochloride; Palonosetron Hydrochloride

Database IDs

• CAS Number: 135729-76-9; 135729-75-8
• PubChem SID: 164232120
• PubChem CID: 18651161

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.109810375
• LogD (pH = 7.4): 1.8701022
• Log P: 2.5460126
• Molar Refractivity: 88.5213 cm^3
• Polarizability: 33.791428 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: 5HT(3) receptor antagonist

Product Information

• Salt Data: HCl
• Application(s): Antiemetic used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV)

DETAILS

Toronto Research Chemicals - P165810

The (S,R)-enantiomer of Palonosetron (P165800), a potent and selective antagonist, with 5-HT3 receptor in vitro. An impurity of Palonosetron.

REFERENCES

• Clark, R.D., et al.: J. Med. Chem., 36, 2645 (1993)
• Wong, E.H.F., et al.: Br. J. Pharmacol., 114, 851 (1993)
• Grunberg, S.M., et al.: Expert. Opin. Pharmacother., 4, 2297 (1993)
• Eisenberg, P., et al.: Ann. Oncol., 15, 330 (1993)
• Siddiqui, M.A.A., et al
• Eur. Pat., 1991, Syntex, 430 190; CA, 115, 114377b, (synth, pharmacol)
• Costall, B. et al., Eur. J. Pharmacol., 1993, 234, 91, (pharmacol)
• Clark, R.D. et al., J. Med. Chem., 1993, 36, 2645-2657, (synth, pharmacol, pmr, cryst struct)
• Wong, E.H.F. et al., J. Neurochem., 1993, 60, 921; 61, 1927, (pharmacol)
• Eglen, R.M. et al., J. Pharmacol. Exp. Ther., 1993, 266, 535, (pharmacol)
• Wong, E.H.F. et al., Br. J. Pharmacol., 1995, 114, 851-859; 860-866, (pharmacol)
• Graul, A. et al., Drugs of the Future, 1996, 21, 906-910, (rev, synth, pharmacol)
• Kowalczyk, B.A. et al., Synthesis, 1996, 816-818; 2000, 1113-1116, (synth, ir, pmr, cmr)
• Kowalczyk, B.A. et al., Org. Process Res. Dev., 1997, 1, 117-120, (synth)